Identification

Name
Diphenhydramine
Accession Number
DB01075  (APRD00587, DB06975)
Type
Small Molecule
Groups
Approved, Investigational
Description

Diphenhydramine, also known commercially as Benadryl, is a first generation antihistamine that is used primarily for the treatment of seasonal allergies. However, it also has antiemetic, antitussive, hypnotic, and antiparkinson properties. As histamine receptors exist both peripherally and in the central nervous system, diphenhydramine has been shown to cause sedation due to its competitive antagonism of histamine H1 receptors within the central nervous system. While its use in in allergies has largely fallen out of favour due to this sedative effect, diphenhydramine has been repurposed for use within many OTC (over the counter) cough-and-cold medications that have been marketed for "night time" use.

Diphenhydramine is also used in combination with 8-chlorotheophylline as the anti-nausea drug Dimenhydrinate where it is utilized primarily for its antagonism of H1 histamine receptors within the vestibular system [4].

Diphenhydramine has also been shown to be implicated in a number of neurotransmitter systems that affect behaviour including dopamine, norepinephrine, serotonin, acetylcholine, and opioid [3]. As a result, diphenhydramine is being investigated for its anxiolytic and anti-depressant properties.

Structure
Thumb
Synonyms
  • 2-(Benzhydryloxy)-N,N-dimethylethylamine
  • 2-diphenylmethoxy-N,N-demthylethanamine
  • alpha-(2-Dimethylaminoethoxy)diphenylmethane
  • beta-Dimethylaminoethanol diphenylmethyl ether
  • beta-Dimethylaminoethyl benzhydryl ether
  • Difenhidramina
  • Diphenhydraminum
  • N-(2-(Diphenylmethoxy)ethyl)-N,N-dimethylamine
  • O-benzhydryldimethylaminoethanol
  • β-dimethylaminoethyl benzhydryl ether
Product Ingredients
IngredientUNIICASInChI Key
Diphenhydramine citrate4OD433S20988637-37-0SPCKHVPPRJWQRZ-UHFFFAOYSA-N
Diphenhydramine hydrochlorideTC2D6JAD40147-24-0PCHPORCSPXIHLZ-UHFFFAOYSA-N
Diphenhydramine methylbromideUJO67AO8YI31065-89-1BDQPXVWYFLTETB-UHFFFAOYSA-M
Diphenhydramine salicylate707L3YC54L7491-10-3RTSZUSOHOIFYSY-UHFFFAOYSA-N
Active Moieties
NameKindUNIICASInChI Key
Phenolunknown339NCG44TV108-95-2ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BenadrylInjection, solution50 mg/1mLIntramuscular; IntravenousParke Davis Div Of Pfizer Inc1957-12-302007-01-31Us
BenadrylInjection, solution50 mg/1mLIntramuscular; IntravenousParke Davis Div Of Pfizer Inc1947-03-062008-01-31Us
Benadryl Inj. 50mg/mlLiquid50 mgIntramuscular; IntravenousWarner Lambert Canada Inc.1994-12-312000-11-27Canada
Diphenhydramine HCl Inj USP 50mg/mlLiquid50 mgIntravenousInternational Medication Systems, Limited1974-12-311997-08-15Canada
Diphenhydramine HCl Injection, USPSolution50 mgIntramuscular; IntravenousSterimax Inc1994-12-31Not applicableCanada
Diphenhydramine Hydrochloride InjectionSolution50 mgIntramuscular; IntravenousFresenius Kabi2012-02-17Not applicableCanada
Diphenhydramine Hydrochloride Injection USPLiquid50 mgIntramuscular; IntravenousSandoz Canada Incorporated1983-12-31Not applicableCanada
Diphenist 50mg/mlLiquid50 mgIntramuscular; IntravenousOmega Laboratories Ltd1997-10-28Not applicableCanada
Scheinpharm Diphenhydramine Inj.50mg/mlSolution50 mgIntramuscular; IntravenousSchein Pharmaceutical Canada Inc.1996-09-302004-07-26Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Diphendydramine HydrochlorideCapsule25 mg/1OralRemedy Repack2010-12-172017-04-24Us66424 0020 01 nlmimage10 1a038d6c
DiphenhydramineInjection, solution50 mg/1mLIntravenousRemedy Repack2013-11-182017-01-20Us
DiphenhydramineInjection, solution50 mg/1mLIntramuscular; IntravenousFresenius Kabi2002-08-01Not applicableUs
Diphenhydramine HydrochlorideCapsule50 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs53808 023820180907 15195 kublxx
Diphenhydramine HydrochlorideInjection, solution50 mg/1mLIntramuscular; IntravenousFresenius Kabi2013-03-26Not applicableUs
Diphenhydramine HydrochlorideCapsule50 mg/1OralRemedy Repack2013-03-252014-03-25Us
Diphenhydramine HydrochlorideCapsule50 mg/1OralMylan Institutional2011-08-232013-12-31Us
Diphenhydramine HydrochlorideInjection50 mg/1mLIntramuscular; IntravenousNucare Pharmaceuticals,inc.1972-11-27Not applicableUs
Diphenhydramine HydrochlorideInjection, solution50 mg/1mLIntramuscular; IntravenousMylan Institutional LLC2013-05-09Not applicableUs
Diphenhydramine HydrochlorideInjection, solution50 mg/1mLIntramuscular; IntravenousGeneral Injectables & Vaccines2017-06-13Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
7 Select AllergyTablet25 mg/1Oral7 Eleven2014-04-22Not applicableUs
7 Select Allergy ChildrensSolution12.5 mg/5mLOral7 Eleven2014-08-05Not applicableUs
7 Select Night Time Sleep AidSolution50 mg/30mLOral7 Eleven2014-04-22Not applicableUs
Adult AllergySolution50 mg/20mLOralChain Drug Consortium2015-05-04Not applicableUs
Adult Allergy ReliefSolution50 mg/20mLOralWalmart Stores2017-05-03Not applicableUs
After Bite OutdoorGel20 mg/1mLTopicalTender Corporation2016-11-012018-03-01Us
After Bite OutdoorGel20 mg/1gTopicalTender Corporation2018-03-01Not applicableUs
After Bite PlusGel20 mg/1gTopicalTender Corporation2018-03-01Not applicableUs
After Bite PlusCream20 mg/1mLTopicalTender Corporation2012-07-032018-03-06Us
After Bite XtraGel20 mg/1gTopicalTender Corporation2018-03-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
7 Select Ibuprofen PMDiphenhydramine citrate (38 mg/1) + Ibuprofen (200 mg/1)Tablet, film coatedOral7 Eleven2014-08-05Not applicableUs
7 Select Night Time Severe Cold Cough and FluDiphenhydramine hydrochloride (25 mg/1) + Acetaminophen (650 mg/1) + Phenylephrine hydrochloride (10 mg/1)Powder, for solutionOral7 Eleven2016-01-25Not applicableUs
7 Select Night Time severe cold, cough and fluDiphenhydramine hydrochloride (25 mg/1) + Acetaminophen (650 mg/1) + Phenylephrine hydrochloride (10 mg/1)Powder, for solutionOral7 Eleven2015-11-122017-08-01Us
7 Select Pain Relief PMDiphenhydramine hydrochloride (25 mg/1) + Acetaminophen (500 mg/1)Tablet, film coatedOral7 Eleven2014-09-042016-07-22Us
7-Select Advil PMDiphenhydramine citrate (38 mg/1) + Ibuprofen (200 mg/1)Tablet, coatedOralLil' Drug Store Products, Inc.2011-06-012017-12-31Us
Aceta-gesicDiphenhydramine hydrochloride (12.5 mg/1) + Acetaminophen (325 mg/1)Tablet, coatedOralRemedy Repack2014-08-08Not applicableUs
Aceta-gesicDiphenhydramine hydrochloride (12.5 mg/1) + Acetaminophen (325 mg/1)Tablet, coatedOralRugby2014-06-30Not applicableUs
AcetadrylDiphenhydramine hydrochloride (25 mg/1) + Acetaminophen (500 mg/1)Tablet, film coatedOralAidarex Pharmaceuticals LLC2011-07-21Not applicableUs
AcetadrylDiphenhydramine hydrochloride (25 mg/1) + Acetaminophen (500 mg/1)Tablet, film coatedOralPhysicians Science & Nature Inc.2011-07-212016-05-31Us
Acetaminophen / Diphenhydramine 500/25 mgDiphenhydramine hydrochloride (25 mg/1) + Acetaminophen (500 mg/1)TabletOralReliable 1 Laboratories2015-11-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AiracofDiphenhydramine hydrochloride (12.5 mg/5mL) + Codeine phosphate hemihydrate (7.5 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)LiquidOralCenturion Labs2010-01-082016-05-02Us
BenadrylDiphenhydramine hydrochloride (50 mg/1mL)Injection, solutionIntramuscular; IntravenousPhysicians Total Care, Inc.2006-01-132010-12-29Us
BenadrylDiphenhydramine hydrochloride (50 mg/1mL)Injection, solutionIntramuscular; IntravenousPhysicians Total Care, Inc.1994-06-012010-12-29Us
Contrast Allergy PreMed PackDiphenhydramine hydrochloride (50 mg/50mg) + Prednisone (50 mg/50mg)KitShertech Laboratories, Llc2016-09-13Not applicableUs
DicopanolDiphenhydramine hydrochloride (0.86 g/0.86g)KitOralCalifornia Pharmaceuticals, Llc2016-01-01Not applicableUs
DicopanolDiphenhydramine hydrochloride (0.75 g/0.75g)KitOralFusion Pharmaceuticals LLC2010-02-08Not applicableUs
DiphenMaxDiphenhydramine (25 mg/1) + Phenylephrine (10 mg/1)Tablet, chewableOralRiver's Edge Pharmaceuticals, LLC2008-01-012009-11-09Us
Endal CDDiphenhydramine hydrochloride (10 mg/5mL) + Codeine phosphate hemihydrate (7.5 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)SyrupOralTiber Laboratories2009-12-092009-12-31Us
FIRST BXN MouthwashDiphenhydramine hydrochloride (0.84 mg/1mL) + Lidocaine hydrochloride (6.75 mg/1mL) + Nystatin (6.75 mg/1mL)KitOralCutisPharma, Inc2009-09-08Not applicableUs
FIRST Dukes Mouthwash CompoundingDiphenhydramine hydrochloride (0.525 g/0.525g) + Hydrocortisone (0.06 g/0.06g) + Nystatin (0.6 g/0.6g)KitOralCutisPharma, Inc.2010-12-15Not applicableUs
International/Other Brands
Aleryl / Alledryl / Allerdryl (Valeant) / Baramine / Beldin / Belix / Benylan (Biogen) / Dermodrin (Montavit) / Desentol (Meda) / Dibondrin (Montavit) / Dimedrol (Zdorovie) / Diphen (Wockhardt) / Dormarex 2 / Genahist / Histaxin (Meda) / Hyrexin (Hyrex) / Nytol Quickgels (GlaxoSmithKline) / Restamin (Kowa Souyaku) / Siladryl / Silphen Cough
Categories
UNII
8GTS82S83M
CAS number
58-73-1
Weight
Average: 255.3547
Monoisotopic: 255.162314299
Chemical Formula
C17H21NO
InChI Key
ZZVUWRFHKOJYTH-UHFFFAOYSA-N
InChI
InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3
IUPAC Name
[2-(diphenylmethoxy)ethyl]dimethylamine
SMILES
CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication

For the treatment of symptoms associated with Vertigo/Meniere's disease, nausea and vomiting, motion sickness and insect bite.

Associated Conditions
Pharmacodynamics

Diphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, diphenhydramine competes with free histamine for binding at HA-receptor sites. Diphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of diphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.

Mechanism of action

Diphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
UMuscarinic acetylcholine receptor M2
antagonist
Human
Absorption

Quickly absorbed with maximum activity occurring in approximately one hour.

Volume of distribution
Not Available
Protein binding

98 to 99%

Metabolism

Hepatic and renal

Route of elimination

Little, if any, is excreted unchanged in the urine; most appears as the degradation products of metabolic transformation in the liver, which are almost completely excreted within 24 hours.

Half life

1-4 hours

Clearance
Not Available
Toxicity

LD50=500 mg/kg (orally in rats). Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular dysrhythmias, coma and death.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Diphenhydramine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(2-benzhydryloxyethyl)diethyl-methylammonium iodideThe risk or severity of adverse effects can be increased when Diphenhydramine is combined with (2-benzhydryloxyethyl)diethyl-methylammonium iodide.
1,10-PhenanthrolineThe therapeutic efficacy of Diphenhydramine can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Diphenhydramine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Diphenhydramine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of serotonin syndrome can be increased when Diphenhydramine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
Food Interactions
  • Avoid alcohol.
  • Take with food.

References

Synthesis Reference

Alison B. Lukacsko, Joseph J. Piala, "Effect of a combination of a terbutaline, diphenhydramine and ranitidine composition on gastrointestinal injury produced by nonsteroidal anti-inflammatory compositions." U.S. Patent US5260333, issued December, 1983.

US5260333
General References
  1. Raphael GD, Angello JT, Wu MM, Druce HM: Efficacy of diphenhydramine vs desloratadine and placebo in patients with moderate-to-severe seasonal allergic rhinitis. Ann Allergy Asthma Immunol. 2006 Apr;96(4):606-14. [PubMed:16680933]
  2. Abdi A, Rose E, Levine M: Diphenhydramine overdose with intraventricular conduction delay treated with hypertonic sodium bicarbonate and i.v. lipid emulsion. West J Emerg Med. 2014 Nov;15(7):855-8. doi: 10.5811/westjem.2014.8.23407. Epub 2014 Sep 19. [PubMed:25493135]
  3. Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [PubMed:11835984]
  4. Jaju BP, Wang SC: Effects of diphenhydramine and dimenhydrinate on vestibular neuronal activity of cat: a search for the locus of their antimotion sickness action. J Pharmacol Exp Ther. 1971 Mar;176(3):718-24. [PubMed:4329456]
External Links
Human Metabolome Database
HMDB0001927
KEGG Drug
D00300
KEGG Compound
C06960
PubChem Compound
3100
PubChem Substance
46505484
ChemSpider
2989
BindingDB
50017674
ChEBI
4636
ChEMBL
CHEMBL657
Therapeutic Targets Database
DAP000490
PharmGKB
PA449349
IUPHAR
1224
Guide to Pharmacology
GtP Drug Page
HET
2PM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Diphenhydramine
ATC Codes
D04AA33 — Diphenhydramine methylbromideD04AA32 — DiphenhydramineR06AA02 — DiphenhydramineR06AA52 — Diphenhydramine, combinations
AHFS Codes
  • 04:04.04 — Ethanolamine Derivatives
  • 04:04.00 — First Generation Antihistamines
PDB Entries
2aot
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentAtopic Dermatitis (AD)1
0RecruitingDiagnosticStage IIB Esophageal Cancer / Stage IIB Esophageal Cancer AJCC v7 / Stage III Esophageal Cancer AJCC v7 / Stage IIIA Esophageal Cancer / Stage IIIA Esophageal Cancer AJCC v7 / Stage IIIB Esophageal Cancer / Stage IIIB Esophageal Cancer AJCC v7 / Stage IIIC Esophageal Cancer / Stage IIIC Esophageal Cancer AJCC v71
1Active Not RecruitingTreatmentMultiple Myeloma (MM)1
1Active Not RecruitingTreatmentNeoplasms Malignant1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableTherapeutic Equivalence1
1CompletedBasic ScienceAllergic Rhinitis (AR)1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceNasal Stuffiness1
1CompletedScreeningFibrosis1
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentMajor Depressive Disorder (MDD)1
1CompletedTreatmentPain NOS1
1CompletedTreatmentRestless Legs Syndrome (RLS)1
1Not Yet RecruitingTreatmentMetastatic Colorectal Cancers1
1RecruitingDiagnosticPatients With Suspected Malignancies of the Pituitary Gland1
1RecruitingDiagnosticA Diagnosis of Any Resectable Lung or Pleural Nodule1
1RecruitingTreatmentDiseases of Oesophagus Stomach and Duodenum1
1RecruitingTreatmentGraft Versus Host Disease (GVHD) / Sickle Cell Disorders1
1RecruitingTreatmentPompe's Disease1
1RecruitingTreatmentTransplantation, Liver1
1RecruitingTreatmentTumors, Solid1
1TerminatedNot AvailableHealthy Male Volunteers1
1TerminatedBasic ScienceDrug Metabolism, Poor, CYP2D6-RELATED1
1TerminatedTreatmentAlpha-1 Antitrypsin Deficiency1
1WithdrawnDiagnosticAbdominal Pain (AP) / Gallbladder disorders / Gallstone formation / Jaundice / Pancreatitis1
1, 2CompletedTreatmentKidney Diseases / Transplantation, Kidney1
1, 2CompletedTreatmentLeukemia, Acute Lymphocytic (ALL) / Leukemia, Acute Myelogenous (AML) / Leukemia, Chronic Myelogenous (CML) / Myelodysplastic Syndromes (MDS) / Non-Hodgkin's Lymphoma (NHL)1
1, 2CompletedTreatmentPost-Traumatic Headaches1
1, 2Not Yet RecruitingTreatmentTumors, Solid1
1, 2RecruitingTreatmentAdult Living Donor Kidney Transplant Recipients / Living Kidney Donors / Transplant, Kidney1
1, 2RecruitingTreatmentLiver Transplant Recipients / Living Donor (of the Respective Liver Transplant Recipient)1
1, 2RecruitingTreatmentLung Cancers1
1, 2TerminatedTreatmentColo-rectal Cancer / Colon/Rectal Cancer / Colon/Rectal Cancer Rectal Cancer / Rectal Carcinoma1
2Active Not RecruitingTreatmentAdvanced Stage Diffuse Large B-Cell Non-Hodgkin's Lymphoma / Non-Hodgkin's Lymphoma (NHL)1
2Active Not RecruitingTreatmentNephritis, Lupus1
2Active Not RecruitingTreatmentRenal Cancers1
2CompletedNot AvailableCancers / Tumors, Solid1
2CompletedSupportive CareStomatitis, Aphthous1
2CompletedTreatmentBlood Cancers / Chronic Lymphocytic Leukaemia (CLL) / Graft Versus Host Disease (GVHD) / Hodgkins Disease (HD) / Leukemias / Malignancies / NHL / Smith-Magenis Syndrome1
2CompletedTreatmentBlood and Marrow Transplant (BMT) / Multiple Myeloma (MM) / Transplantation, Autologous / Transplantation, Homologous1
2CompletedTreatmentCancer, Breast1
2CompletedTreatmentCerebrovascular Accident, Acute / Edema of the cerebrum1
2CompletedTreatmentChronic Idiopathic Urticaria1
2CompletedTreatmentDepression1
2CompletedTreatmentEndometrial Cancers1
2CompletedTreatmentLeukemia, Mast-Cell / Mantle Cell Lymphoma (MCL)1
2CompletedTreatmentLupus Erythematosus, Systemic1
2CompletedTreatmentMalignant Lymphomas1
2CompletedTreatmentMultiple Myeloma (MM)1
2CompletedTreatmentRejection, Transplant1
2CompletedTreatmentRenal Cell Adenocarcinoma1
2CompletedTreatmentRestless Legs Syndrome (RLS)1
2CompletedTreatmentVulvodynia1
2Not Yet RecruitingTreatmentDiabetic Macular Edema (DME)1
2Not Yet RecruitingTreatmentHigh Risk / Newly Diagnosed / Plasma Cell Myeloma1
2RecruitingTreatmentAlcohol Dependence1
2RecruitingTreatmentCocaine-Related Disorders1
2RecruitingTreatmentHNSCC / HPV-Related Squamous Cell Carcinoma1
2RecruitingTreatmentImpaired Renal Function / RrMM1
2RecruitingTreatmentPlasma Cell Myeloma2
2RecruitingTreatmentTransplant, Kidney1
2TerminatedSupportive CareNausea / Unspecified Childhood Solid Tumor, Protocol Specific / Vomiting1
2TerminatedTreatmentBlood and Marrow Transplant (BMT) / Diffuse Large B-Cell / Lymphoma, B-Cell / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Lymphomas: Non-Hodgkin / Malignant Lymphoma, Non-Hodgkin / Non-Hodgkin's Lymphoma (NHL)1
2TerminatedTreatmentHepatitis B Chronic Infection1
2TerminatedTreatmentProstate Cancer1
2TerminatedTreatmentT-cell Type Acute Leukemia-Precursor T-lymphoblastic Lymphoma/Leukaemia1
2TerminatedTreatmentTransplantation, Kidney1
2, 3CompletedTreatmentLupus Erythematosus, Systemic1
2, 3CompletedTreatmentMalaria caused by Plasmodium falciparum1
2, 3CompletedTreatmentVesicular Stomatitis1
2, 3TerminatedTreatmentLupus Erythematosus, Systemic1
3CompletedTreatmentAcute Urticaria1
3CompletedTreatmentChronic Idiopathic Urticaria1
3CompletedTreatmentElective Caesarean Section Surgeries1
3CompletedTreatmentHeadaches / Intranasal Ketamine1
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentMigraines1
3CompletedTreatmentNephritis, Lupus1
3Not Yet RecruitingTreatmentMalaria caused by Plasmodium falciparum1
3RecruitingTreatmentAcute Lymphoblastic Leukemia, Pediatric1
3RecruitingTreatmentAcute Urticaria1
3RecruitingTreatmentPost-Traumatic Headaches1
3RecruitingTreatmentPostoperative pain1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3Unknown StatusTreatmentSleeplessness1
3WithdrawnTreatmentCoughing / Inflammatory Reaction / Rhinitis1
4Active Not RecruitingSupportive CareAdjunct Anesthesia Medication / Colonoscopy1
4CompletedDiagnosticAsthma Bronchial1
4CompletedPreventionHypnotic / Specified Sedative1
4CompletedTreatmentBacterial Infections1
4CompletedTreatmentCough Reflex Sensitivity1
4CompletedTreatmentHeadaches1
4CompletedTreatmentMigraines2
4CompletedTreatmentMigrainous Headache / Nausea / Restlessness1
4CompletedTreatmentNasal Stuffiness1
4CompletedTreatmentExtra-pyramidal symptoms / Nausea1
4CompletedTreatmentNeurogenic Intermittent Claudication / Spinal Stenosis of Lumbar Region1
4CompletedTreatmentOccasional Sleeplessness1
4CompletedTreatmentTrigger Finger Disorder1
4Not Yet RecruitingOtherACL Injury1
4Not Yet RecruitingPreventionPremature Births1
4Not Yet RecruitingSupportive CareDiabetes Mellitus (DM)1
4RecruitingTreatmentHeadaches1
4SuspendedTreatmentMigrainous Headache1
Not AvailableActive Not RecruitingOtherPain NOS1
Not AvailableActive Not RecruitingScreeningAlcoholism1
Not AvailableCompletedBasic ScienceHyperalgesia1
Not AvailableCompletedBasic ScienceMemory, Long-Term / Memory, Short-Term1
Not AvailableCompletedOtherPain, Neuropathic1
Not AvailableCompletedPreventionGeneral Surgery / Pain NOS1
Not AvailableCompletedPreventionHeadaches1
Not AvailableCompletedSupportive CareFocus of Study: Absorption of the Three Components in the Topical ABH Gel in Healthy Volunteers, and Determine if There Are Any Adverse Effects / Healthy Volunteers1
Not AvailableCompletedSupportive CareNausea / Vomiting1
Not AvailableCompletedTreatmentBenign Paroxysmal Positional Vertigo (BPPV)1
Not AvailableCompletedTreatmentEndometriosis1
Not AvailableCompletedTreatmentEndoscopy / Sedation therapy1
Not AvailableCompletedTreatmentHip Fracture Surgery / Post Operative Pain Control1
Not AvailableCompletedTreatmentItching1
Not AvailableCompletedTreatmentPain NOS1
Not AvailableRecruitingTreatmentAlcohol-Related Disorders / Brain Injury / Depression / Disease, Chronic / Mild Cognitive Impairment (MCI) / Pain NOS / Posttraumatic Stress Disorders / Quality of Life / Substance-Related Disorders / Suicidal Ideation / Wounds and Injuries1
Not AvailableRecruitingTreatmentAnxiety Disorders / Moods Disorders / Pain Disorders / Somatization Disorder1
Not AvailableRecruitingTreatmentMigrainous Headache1
Not AvailableSuspendedDiagnosticBulimia Nervosa (BN) / Catechol-O-methyltransferase / Dopamine / Eating Disorders / Reward1
Not AvailableTerminatedNot AvailablePain, Chronic1
Not AvailableTerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentPrimary Headaches (Includes Migraines, Tension, Cluster Headaches)1
Not AvailableUnknown StatusSupportive CareEndoscopic Retrograde Cholangiopancreatography (ERCP) / Endoscopic Ultrasound (EUS)1
Not AvailableWithdrawnTreatmentPost Operative Nausea and Vomiting (PONV) / Rescue Emetic Therapy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Advance Pharmaceutical
  • Advent Pharmaceuticals Inc.
  • Amend
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Auriga Pharmaceuticals LLC
  • Barr Pharmaceuticals
  • Baxter International Inc.
  • Bergen Brunswig
  • Bioniche Pharma
  • Bryant Ranch Prepack
  • C.O. Truxton Inc.
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Chattem Chemicals Inc.
  • Concord Labs
  • Consolidated Midland Corp.
  • Contract Pharm
  • CVS Pharmacy
  • Darby Dental Supply Co. Inc.
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • DispenseXpress Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • Equaline Vitamins
  • Fusion Pharmaceuticals LLC
  • General Injectables and Vaccines Inc.
  • GlaxoSmithKline Inc.
  • Goldline Laboratories Inc.
  • Group Health Cooperative
  • Hawthorn Pharmaceuticals
  • Heartland Repack Services LLC
  • Hospira Inc.
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Kraft Pharmaceutical Co. Inc.
  • Liberty Pharmaceuticals
  • Lnk International Inc.
  • Major Pharmaceuticals
  • Martin Surgical Supply
  • McNeil Laboratories
  • Medique Products
  • Medtech Labs
  • Merit Pharmaceuticals
  • Midlothian Labs
  • Mississippi State Dept Health
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nexgen Pharma Inc.
  • North Safety Products
  • Nucare Pharmaceuticals Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pfizer Inc.
  • Pharmaceutical Association
  • Pharmedix
  • Physicians Total Care Inc.
  • Poly Pharmaceuticals Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Procter & Gamble
  • Provident Pharmaceuticals LLC
  • Remedy Repack
  • Rite Aid Corp.
  • River's Edge Pharmaceuticals
  • Rugby Laboratories
  • Sandhills Packaging Inc.
  • Scientific Laboratories Inc.
  • Silarx Pharmaceuticals
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Tya Pharmaceuticals
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Walgreen Co.
Dosage forms
FormRouteStrength
KitTopical
Capsule; kitOral
CapsuleOral
CreamTopical20 mg/1mL
CreamTopical2.0 mL/100mL
LiquidOral12.5 mg/5mL
Capsule, gelatin coatedOral
PowderOral25 mg/1
CreamTopical
LiquidOral12.5 mg
SolutionOral12.5 mg
GelTopical2 g/100g
CreamTopical2.0 %
PatchTopical
Injection, solutionIntramuscular; Intravenous50 mg/1mL
TabletOral25 mg
StripOral25 mg/1
Tablet, chewableOral12.5 mg
LiquidTopical
LiquidOral6.25 mg
CreamTopical2 %
ElixirOral12.5 mg
GelTopical20 mg/1mL
Tablet, chewableOral25 mg
GelTopical2 %
SprayTopical
TabletOral25 mg/250mg
StripOral25 mg
SyrupOral
LotionTopical
SuspensionTopical
LiquidOral
Tablet, coatedOral25 mg/ 11
SyrupOral6.25 mg
TabletOral19 mg
StripOral19 mg
SuspensionOral
TabletOral12.5 mg/1
Tablet, chewableOral12.5 mg/1
Kit; tabletOral
OintmentTopical
Powder, for solutionOral
GelTopical
KitOral0.75 g/0.75g
KitOral0.86 g/0.86g
TabletOral38.0 mg
Capsule, coatedOral25 mg/1
Injection, solutionIntravenous50 mg/1mL
Capsule, liquid filledOral20 mg/1
TabletOral50 mg/1
LiquidIntravenous50 mg
CapsuleOral25 mg/1
CapsuleOral50 mg/1
Capsule, liquid filledOral50 mg/1
ElixirOral25 mg/10mL
InjectionIntramuscular50 mg/1mL
InjectionIntramuscular; Intravenous50 mg/1mL
InjectionParenteral50 mg/1mL
SolutionOral25 mg/10mL
SolutionOral50 mg/20mL
Tablet, coatedOral25 mg/1
Tablet, film coatedOral25 mg/1
LiquidIntramuscular; Intravenous50 mg
Tablet, chewableOral
KitOral; Topical
Capsule, liquid filledOral
Capsule, liquid filledOral25 mg/1
SolutionOral50 mg/40mL
KitOral
Aerosol, sprayTopical
LiquidTopical20.3 g/1L
SprayTopical2 g/100mL
GelTopical2.03 g/100g
AerosolTopical
SolutionTopical
StripOral12.5 mg
TabletOral12.5 mg
Tablet, orally disintegratingOral12.5 mg/1
LinimentTopical
Capsule, gelatin coatedOral50 mg/1
Kit
LozengeOral25 mg
StripOral
SolutionOral50 mg/30mL
CapsuleOral25 mg
LiquidOral50 mg/30mL
SolutionOral50 mg
Tablet, film coatedOral50 mg/1
PowderOral
SolutionOral
TabletOral50 mg
Granule, for solutionOral
Tablet, coatedOral
ElixirOral2.5 mg
SolutionOral12.5 mg/5mL
SyrupOral12.5 mg/5mL
GelTopical20.5 mg/1mL
PlasterTopical
SolutionIntramuscular; Intravenous50 mg
GelTopical2 g/100mL
GelTopical.2 g/10mL
TabletOral
Tablet, coatedOral50 mg/1
Tablet, multilayerOral
Tablet, multilayer, extended releaseOral
GelTopical20 mg/1g
SprayTopical20 mg/1mL
Capsule, coatedOral
TabletOral25 mg/1
Tablet, film coatedOral
CapsuleOral50 mg
Tablet, chewableOral25 mg/1
LiquidOral6.25 mg/1mL
LiquidOral25 mg/10mL
Capsule, gelatin coatedOral50 mg/21
SprayTopical2.0 %
Capsule, liquid filledOral50 mg/21
LiquidOral50 mg
Capsule, gelatin coatedOral25 mg/1
Prices
Unit descriptionCostUnit
DiphenhydrAMINE HCl 100 50 mg capsule Bottle13.99USD bottle
Diphenhydramine 50 mg/ml3.94USD ml
Diphenhydramine 50 mg/ml vial1.69USD ml
DiphenhydrAMINE HCl 50 mg/ml vial1.44USD vial
Dytan 25 mg tablet chewable1.37USD tablet
Benadryl 50 mg/ml vial1.36USD ml
Diphenmax 25 mg tablet1.24USD tablet
Benadryl allergy 25 mg strips0.45USD strip
Unisom sleep aid tablet0.34USD tablet
Sleep-eze 3 tablet0.29USD tablet
Compoz 50 mg tablet0.27USD tablet
Sominex max str 50 mg caplet0.27USD caplet
Benadryl allergy fastmelt tablet0.26USD tablet
Unisom 25 mg sleeptabs0.25USD tablet
Unisom 50 mg sleepgels0.25USD each
Unisom sleepmelts 25 mg tablet0.24USD tablet
Nytol 25 mg tablet0.23USD tablet
Benadryl allergy-sinus caplet0.22USD caplet
Compoz 25 mg gelcap0.2USD capsule
Benadryl allergy 25 mg softgel0.19USD softgel capsule
Benadryl allergy 25 mg ultratab0.19USD tablet
Benadryl allergy-cold kapgels0.19USD each
Benadryl allergy-sinus kapgels0.19USD each
Benadryl-d allergy-sinus ultratab0.19USD tablet
Diphenhydramine hcl powder0.17USD g
Eql allergy 25 mg tablet0.17USD tablet
Nighttime sleep aid 25 mg cplt0.17USD caplet
Banophen anti-itch 2% cream0.16USD g
Benadryl itch relief stick0.16USD ml
Sominex 25 mg tablet0.16USD tablet
Benadryl allergy 25 mg kapgels0.15USD each
Allergy 25 mg tablet0.14USD tablet
Benadryl 25 mg kapseals0.14USD each
Benadryl itch stopping crm0.14USD g
DiphenhydrAMINE HCl 25 mg capsule0.13USD capsule
Diphenhist with zinc cream0.12USD g
Ra allergy 25 mg tablet0.12USD tablet
CVS Pharmacy allergy 25 mg tablet0.11USD tablet
Diphenhydramine 25 mg minitab0.11USD tablet
Simply sleep 25 mg caplet0.11USD caplet
Sleep ii tablet0.11USD tablet
Diphenhydramine 50 mg capsule0.1USD capsule
Benadryl 2% spray0.09USD ml
Diphenhist 50 mg tablet0.09USD tablet
Genahist 25 mg tablet0.09USD tablet
Ra sleep tablet0.09USD tablet
Banophen 25 mg tablet0.08USD tablet
Wal-dryl anti-itch spray0.08USD ml
CVS Pharmacy allergy 25 mg caplet0.07USD caplet
Nighttime sleep aid 25 mg caplet0.07USD caplet
CVS Pharmacy itch relief spray0.06USD ml
Diphen 25 mg capsule0.06USD capsule
Diphenhist 25 mg caplet0.06USD caplet
Benadryl anti-itch 0.45% gel0.05USD g
Diphenhydramine 50 mg caplet0.05USD caplet
Benadryl itch stopping gel0.04USD g
Child benadryl-d aller-sin liquid0.04USD ml
Diphenhydramine 25 mg capsule0.04USD capsule
Vicks 44d cough & head liquid0.03USD ml
Vicks 44e cough & chest liquid0.03USD ml
Banophen allergy liquid0.02USD ml
Diphenhydramine 25 mg tablet0.02USD tablet
Ra anti-tussive dm syrup0.02USD ml
Siladryl 12.5 mg/5 ml liquid0.02USD ml
Silphen cough syrup0.02USD ml
Silphen dm cough syrup0.02USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8883849No2002-01-172022-01-17Us
US9155718No2002-01-172022-01-17Us
US8263647No2002-05-302022-05-30Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)161-162Martin, H., Hafliger, F.,Gatzi, K.and Grob, A.; U.S. Patent 2,397,799; April 2,1946; assigned to J.R. Geigy AG, Switzerland. Rieveschl, G. Jr.; U.S. Patent 2,421,714; June 3,1947; assigned to Parke, Davis & Co. Rieveschl, G. Jr.; U.S. Patent 2,427,878; September 23,1947; assigned to Parke, Davis & Company.
boiling point (°C)150-165 °C at 2.00E+00 mm HgPhysProp
water solubility3060 mg/L (at 37 °C)BEILSTEIN
logP3.27HANSCH,C ET AL. (1995)
pKa8.98SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0752 mg/mLALOGPS
logP3.44ALOGPS
logP3.65ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.93 m3·mol-1ChemAxon
Polarizability29.86 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9898
Blood Brain Barrier+0.9381
Caco-2 permeable+0.8744
P-glycoprotein substrateSubstrate0.6211
P-glycoprotein inhibitor INon-inhibitor0.6632
P-glycoprotein inhibitor IINon-inhibitor0.8381
Renal organic cation transporterInhibitor0.7752
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.6173
CYP450 1A2 substrateInhibitor0.8306
CYP450 2C9 inhibitorNon-inhibitor0.9144
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9039
CYP450 3A4 inhibitorNon-inhibitor0.934
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7293
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6495
BiodegradationNot ready biodegradable0.9253
Rat acute toxicity2.7846 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.536
hERG inhibition (predictor II)Inhibitor0.6318
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9100000000-7b9eb1f702c76f6b6062
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9200000000-b9014c8fc8ccbba24163
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-0006-0090000000-a71e531b49571f09ab25
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-00kk-0980000000-cce91896f34562beeffa
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-001i-1900000000-4c29bd5e0eab94596eaa
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-0a4i-9100000000-ab642e8f86de11af896c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000t-0910000000-3576ca5ec77ab87354ec
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-0ccd6de9ca58593fd490
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-3568aae4c27ffe333c0e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-22e0c745355c836f1535
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-6bb69a66a343440c64f8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-1b87d83415d22bb17f1b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0gb9-0900000000-50251362d768cd1b1c4f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0gb9-0900000000-9f37a733a05f5b01d313
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-7d73b95ed09ea2d72260
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0gb9-2900000000-1666a8ab5a6d81c0bd01
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-3f31841d858381760f03
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-de872e048c7e12cef490
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-de872e048c7e12cef490
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0900000000-789a4a3fe118d5bf2456
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-2900000000-8ef94659f614b9ff24ca
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-2950000000-7c7a9841f2f0b6428d69
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Benzylethers / Trialkylamines / Dialkyl ethers / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Diphenylmethane / Benzylether / Tertiary aliphatic amine / Tertiary amine / Ether / Dialkyl ether / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amino compound, ether (CHEBI:4636) / a small molecule (CPD-10890)

Targets

Details
1. Histamine H1 receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Piao H, Nagai S, Tsurumaki T, Niki T, Higuchi H: Potentiation by neuropeptide Y of histamine H1 receptor-mediated contraction in rat blood vessels. Vascul Pharmacol. 2007 Apr;46(4):260-70. Epub 2006 Oct 27. [PubMed:17169617]
  3. Kesiova M, Alexandrova A, Yordanova N, Kirkova M, Todorov S: Effects of diphenhydramine and famotidine on lipid peroxidation and activities of antioxidant enzymes in different rat tissues. Pharmacol Rep. 2006 Mar-Apr;58(2):221-8. [PubMed:16702624]
  4. Hasala H, Moilanen E, Janka-Junttila M, Giembycz MA, Kankaanranta H: First-generation antihistamines diphenhydramine and chlorpheniramine reverse cytokine-afforded eosinophil survival by enhancing apoptosis. Allergy Asthma Proc. 2007 Jan-Feb;28(1):79-86. [PubMed:17390763]
  5. Wang Z, Woolverton WL: Self-administration of cocaine-antihistamine combinations: super-additive reinforcing effects. Eur J Pharmacol. 2007 Feb 28;557(2-3):159-60. Epub 2006 Dec 1. [PubMed:17196194]
  6. Ishikawa T, Takechi K, Rahman A, Ago J, Matsumoto N, Murakami A, Kamei C: Influences of histamine H1 receptor antagonists on maximal electroshock seizure in infant rats. Biol Pharm Bull. 2007 Mar;30(3):477-80. [PubMed:17329841]
  7. Havas TE, Cole P, Parker L, Oprysk D, Ayiomamitis A: The effects of combined H1 and H2 histamine antagonists on alterations in nasal airflow resistance induced by topical histamine provocation. J Allergy Clin Immunol. 1986 Nov;78(5 Pt 1):856-60. [PubMed:2878016]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Liu H, Zheng Q, Farley JM: Antimuscarinic actions of antihistamines on the heart. J Biomed Sci. 2006 May;13(3):395-401. [PubMed:16453179]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [PubMed:9616188]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Connecticut's Official State Website: CYP Chart [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2018 20:29